Potassium Carbonate → Ethyl 5-bromo-4-methylbenzofuran-2-carboxylate

HRID 2036045Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=O.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19].CCCCCC>CN(C=O)C>[CH2:22]([O:21][C:18]([C:19]1[O:10][C:7]2[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([CH3:11])[C:4]=2[CH:5]=1)=[O:20])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-Bromo-6-hydroxy-2-methyl-benzaldehyde (6.8 g, 0.032 mol)) in anhydrous DMF (50 ml) was added potassium carbonate (13.1 g, 0.095 mol) and cooled to 0° C. Bromo ethyl acetate (7.1 ml, 0.063 mol) was added slowly. The reaction mixture was stirred for one hour at 0° C. The completion of the reaction was confirmed by TLC. The reaction mixture was then heated to 100° C. and maintained for 2 hours. After cooling to room temperature, ice water (250 ml) was added and the mixture was stirred for 20 minutes. The solid separated was filtered, washed with water (100 ml) and dried under vacuum, to get crude product. Column chromatography using 2/5 ethyl acetate/hexane yielded 5-Bromo-4-methyl-benzofuran-2-carboxylic acid ethyl ester (6.2 g, 69.6%)

Workup

temperatureThe reaction mixture was then heated to 100° C.
temperaturemaintained for 2 hours
temperatureAfter cooling to room temperature
stirringthe mixture was stirred for 20 minutes
customThe solid separated
filtrationwas filtered
washwashed with water (100 ml)
customdried under vacuum
customto get crude product

Sources & evidence

ORD record: ord-33df53f91abf4461ab2a4da271676688
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575161B2

Reaction notes

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